Journal article
Enantiopure Trans-4,5-Disubstituted 2-Imidazolidinones via Copper(I)-Catalyzed Ring Opening of 1,1 '-DiBoc-2,2 '-Biaziridine with Grignard Reagents
Journal of Organic Chemistry, Vol.80(11), pp.5992-5998
2015
PMID: 25938909
Abstract
The copper-catalyzed ring opening of chiral-pool-derived 1,1'-diBoc-2,2'-biaziridine with Grignard reagents affords enantiopure 2-imidazolidinones in a desymmetrizing, cascade process involving the Boc protecting group. This divergent strategy provides reaction-ready, N-differentiated products and allows two C-C bond constructions concurrent to imidatolidinone formation. A variety of alkyl, cyclic, and aryl Grignard reagents are tolerated in reasonable to good yields.
Details
- Title
- Enantiopure Trans-4,5-Disubstituted 2-Imidazolidinones via Copper(I)-Catalyzed Ring Opening of 1,1 '-DiBoc-2,2 '-Biaziridine with Grignard Reagents
- Authors
- Matthew D. Kennedy (Author) - University of WollongongStephen J. Bailey (Author) - University of WollongongSteven M. Wales (Author) - University of WollongongPaul A. Keller (Author) - University of Wollongong
- Publication details
- Journal of Organic Chemistry, Vol.80(11), pp.5992-5998
- Publisher
- American Chemical Society
- DOI
- 10.1021/acs.joc.5b00832
- ISSN
- 1520-6904
- PMID
- 25938909
- Organisation Unit
- Student Services and Engagement; School of Science, Technology and Engineering
- Language
- English
- Record Identifier
- 99707484502621
- Output Type
- Journal article
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- Chemistry, Organic
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